Crosswinds Advisors is a practitioner-led enterprise transformation advisory firm founded on one belief: organizations navigating digital transformation deserve someone who has actually led it — not someone selling a framework. Every engagement is built around your specific reality. No playbooks. No generic slide decks. Just hard-won expertise from the C-suite, applied directly to your context.
About Crosswinds Advisors
Sandip Sahota
Founder
Sandip spent 28 years leading enterprise transformation at some of the world's most complex financial institutions — Morgan Stanley, CPP Investments, Bank of New York Mellon and BMO — before founding Crosswinds Advisors in 2025.
At BMO, he served as Senior Vice President and Enterprise Chief Data and Analytics Officer and member of the Technology and Operations Executive Committee. He led the wholesale reinvention of the Bank's enterprise technology and data capability — building a 725-person organization from a 45-person function, driving BMO's Digital First agenda across 55,000+ employees and 8 million customers, and directing the data and technology integration of the largest acquisition in Canadian banking history: Bank of the West (US$16.3B), seamlessly integrating approximately 2 million customers and 2.5 petabytes of data into the BMO digital and technology ecosystem.
Prior to BMO, Sandip was Managing Director and Head of Data and Solutions at Bank of New York Mellon, recruited directly onto the incoming COO's leadership team to lead a large-scale digital and data transformation across global operations — a 1,000-person organization spanning 20 cities worldwide. Before that, he served as Managing Director and Head of Enterprise Data and Services at CPP Investments, where he built a next-generation data and analytics capability within a ~C$675B global investment platform. His career began with 15 years at Morgan Stanley, where he progressed from Product Manager to Executive Director and COO of the Enterprise Data Group, ultimately accountable for ~US$200M in core data products, technology services and analytical assets. That career — five institutions, three countries, mandates ranging from operating model redesign to billion-dollar acquisition integration — is the foundation every Crosswinds engagement is built on.
Sandip is the recipient of the Informatica 2022 Chief Data Officer Award and a nominated member of World 50 for Data and Analytics.
In 2025, Sandip founded Crosswinds Advisors and enrolled in the Global Executive MBA program at the Kellogg School of Management at Northwestern University and the Schulich School of Business at York University — because the best practitioners never stop learning.
Crosswinds currently serves clients spanning investment management, capital markets and financial services.
📩 sandip@crosswindsadvisors.com
📞 905-483-3772